Reversible solid-state interconversion of rhodizonic acid H2C6O6 into H6C6O8 and the solid-state structure of the rhodizonate dianion C6O62- (aromatic or non-aromatic?)

被引:26
作者
Braga, D
Cojazzi, G
Maini, L
Grepioni, F
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, CNR, Ctr Fis Macromol, I-40126 Bologna, Italy
[2] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1039/b107317f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anhydrous rhodizonic acid H2C6O6 is obtained by (fully reversible) thermal dehydration of solid 2,3,5,5,6,6-hexahydroxycyclohex-2-ene 1,4-dione, H6C6O8, commonly known as rhodizonic acid dihydrate. Treatment of H6C6O8 with RbOH yields crystals of Rb2C6O6; the oxocarbon dianion C6O62- is shown to possess a flat, benzene-type structure, with C-C bonds shorter than expected for a (non-aromatic) ketonic-type structure.
引用
收藏
页码:1221 / 1223
页数:3
相关论文
共 34 条
[1]   ARE THE OXOCARBON DIANIONS REALLY AROMATIC [J].
AIHARA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) :1633-1635
[2]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[3]   VIBRATIONAL SPECTRA AND STRUCTURE OF RHODIZONATE DIANION [J].
BAILEY, RT .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (04) :627-&
[4]  
Bartsch MR, 1996, J FORENSIC SCI, V41, P1046
[5]  
Braga D, 2000, CHEM-EUR J, V6, P1310, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1310::AID-CHEM1310>3.3.CO
[6]  
2-K
[7]   Intermolecular interactions in nonorganic crystal engineering [J].
Braga, D ;
Grepioni, F .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (09) :601-608
[8]  
Braga D, 2000, CHEM-EUR J, V6, P4536, DOI 10.1002/1521-3765(20001215)6:24<4536::AID-CHEM4536>3.3.CO
[9]  
2-D
[10]   On the charge delocalisation in partially deprotonated polycarboxylic acid anions and zwitterions forming (-)O-H•••O(-) interactions in the solid state [J].
Braga, D ;
Novoa, JJ ;
Grepioni, F .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (02) :226-230